Preheat oven to 350 degrees F. Line a large baking sheet with a Silpat baking mat and set aside.
In a small bowl, combine the sugar and orange zest. Rub together with your fingers until fragrant. In the bowl of a stand mixer, beat the butter and sugar mixture until fluffy, about 3 minutes. Add the egg and vanilla extract and beat until incorporated.
In a medium bowl, whisk together the flour and salt. Gradually add the dry ingredients to the wet ingredients. Mix until combined. Wrap the dough in plastic wrap and chill for 30 minutes.
Scrape some of the dough into your cookie press that has been fitted with a decorative plate, following manufacturer’s instructions. I used a tree shape. Hold the cookie press perpendicular to the prepared baking sheet, with the tip almost touching the sheet, and squeeze the trigger. Continue to press out the cookies, spacing about 1 inch apart.
Bake cookies for about 8 minutes or just until the edges are barely tinged with brown. Remove from the oven and gently transfer the cookies to a wire rack to cool completely.
Melt the chocolate chips in the microwave, stirring every 30 seconds until melted and smooth. Place the cookies on parchment paper and drizzle lightly with melted chocolate. Let the cookies set until chocolate hardens.
Note-the cookies will keep in an airtight container on the counter for up to 5 days.